We've Got A Lot To Learn
by TalkingToTulips
Summary: You know you're destined to be when the King and Queen of Manhattan are trying to get you together, and won't stop until they succeed. The Basses don't fail at what's inevitable. St Berry/Chair crossover.


**So, in an attempt to catch my muse and bring her back kicking and screaming, I decided to step away from my multi-chapters for a bit and work on a new idea that would give me a challenge. Enter Julie, my amazing beta, who whilst we were discussing the amazing-ness of two people called Blair Waldorf and Chuck Bass and why the hell they're not together at the moment, suggested that I write a fic that featured both Chair and St Berry. Challenge accepted. So this fic is dedicated to Julie, my amazing beta. **

**So, basically this not only fixes the St Berry situation but fixes how abysmal Season Five of Gossip Girl has been since Chuck and Blair were pulled apart and she was married to a guest star then ran off with someone who desperately needs a hair cut. But be warned, for this to work, Rachel and Jesse are both 22 and 24 respectively, whilst Blair and Chuck and 23 and 22 respectively. Meaning all the Season One drama happened in 2008, not 2010. So enjoy the Chair, enjoy the scheming, enjoy the St Berry-ness. Don't forget to tell me what you thought once you're finished, I'd love to hear if this was a complete failure or not. **

**TTTX**

* * *

Blair Waldorf-Bass could tell you she was perfectly content with her life. She'd run away with Chuck. Well, not run off per say, they still lived on the Upper East Side, exactly where they had all their lives. Blair had gone to Louis that night and given back his ring, and then walked out the prince's life forever. With help from her friends, and Chuck, Louis was soon no longer welcome on the Upper East Side to interfere with the happy couple and their baby again. Whilst the baby was technically Louis' child (a sizeably check and non disclosure agreement had brought the royal family's silence on the paternity of the child), the son born 7 months after the engagement was broken off was every bit a Bass and would be raised as such.

Blair and Chuck married a month after they reunited, it was a private ceremony in New York with close friends and family. They honeymooned/babymooned in their suite at The Empire, completely hidden from society for two weeks as Blair didn't want to travel 3, nearly 4 months pregnant and they could easily substitute the sun and sea of Cuba or Hawaii for their bed in the suite. After the two weeks were up, Chuck went back to running the Bass empire and Blair focused on flurry of press and visitors at the Waldorfs (Blair moved back and forth between the suite and her family home throughout the day) when the ceremony somehow (Serena) made itself onto Gossip Girl and everyone on the Upper East Side wanted to congratulate the newly weds and see how Blair was glowing with the beauty of pregnancy.

Five months after the ceremony, Blair went into a 15 hour labour (most of which she spent pacing her room begging Chuck to get Louis on the phone so she could tear him a new one in whatever french she could remember from High School, which he of course declined) and with her mother on one side, and Chuck on the other, the Basses' first son, Henry Bass was born in the late hours on one summery June afternoon. The pair were instantly smitten with the boy, and brought him back to their suite, now complete with the most extravagant and beautiful nursery that any baby could hope for, a few days later. Blair threw herself into mothering her son, with help from her faithful maid, Dorota and Chuck did his fair share of parenting, late night feeds and watching their son during the days when he wasn't nurturing the empire their newborn would one day come to inherit.

Yes, Blair could say she was perfectly happy with her life.

But there was one problem. In the eleven months since their son's birth, Blair had spent an awful lot of her time with Henry and either Dorota or Chuck. She had a serious case of cabin fever, or rather luxury suite fever. And she understood that being a mother was a precious thing, and her son was the apple of her eye, but Henry was a bit dull right now. It had been a month since he'd started crawling and that was the last milestone she'd seen since then.

She needed to get away from her child for a few hours, at least.

"Why don't you go out to lunch with Serena or something?" Chuck asked oh so innocently that morning when Blair brought up the idea of getting out of the suite for the day, and not taking Henry with her. She had planned to leave him with Dorota for the night, the only person she trusted Henry with, besides her mother, of course. Henry definitely liked Dorota, because he hadn't tugged her hair yet. Yes, Blair had trained her son not to touch her hair. Chuck was watching Blair do her makeup in their facing vanity mirrors so they could keep eye contact as they readied for the day. She rolled her eyes and swept the bronzer brush over her delicate cheekbones as Chuck tied his tie and sorted out his shirt for his day of business meetings.

"Because, whilst I have grown since 2010, Serena seems to be backtracking." Blair explained in her typical judgmental tone that he knew so well as she exchanged the bronzer brush for an eyeliner and started applying it. "I'm not leaving my son to hang around another child, Henry's a lot more interesting to be around compared to her. I need to be at a party or function or something. I need a conversation with an adult. The more alcohol involved, the better." She added as she turned her back to her vanity and stood up, padding barefoot over to Chuck's side of the bedroom. A few seconds later, and Chuck could feel his wife wrapping her arms around his midsection and nuzzling her face to his shoulder, which made him smile softly.

"You don't have to ask my permission, Blair. I'm sure Dorota will look after Henry until I get home from the negotiations around 10. Henry's sleeping through the nights now so I can stay here with him and you can go out and have a good time, you deserve it. Let us boys fend for ourselves for once." He assured his wife as he finished with his shirt and turned to envelop Blair in his arms, kissing the top of her head gently as he did. Blair smiled and cuddled closer to his chest. A few seconds later, Chuck pulled away from Blair slightly to walk over to their giant bed where Henry Bass was sat up and attempting to pull his own sock off. Chuck plucked the boy from the duvets and kissed his mane of brunette hair that was unmistakably Blair's. The boy instantly became enamored in his Daddy's butterscotch yellow sleeves and began pulling at the fabric with curiosity. "We'll be fine while Mummy parties, won't we, Henry?" He asked the boy with a chuckle.

"Stop being cute with our son, or I won't want to go." Blair retorted playfully, pointing her finger at her husband with mock judgement as she approached her two boys and straightened out Henry's hair, kissing his forehead. "Mummy loves you, Henry but as an inhabitant of the Upper East Side, she sometimes has the uncontrollable urge to sip champagne and make petty small talk with people about their yachts and summer homes. You'll understand one day, your father and I are champions at pretending to care about other people's yachts and summer homes." She informed her son softly. Chuck smirked and nodded with his wife's words and quickly checked his watch. He regretfully announced that the car was waiting for him and handed Henry to Blair. He pressed his lips tenderly to Blair's and warned her not to drink too much champagne tonight with a smile before taking his briefcase, a one year anniversary gift from Blair herself, and started towards the elevator that separated the Bass family from reality, leaving Blair to plan her escape from motherhood.

* * *

It was easier to find somewhere to go for the night than Blair had thought, a quick word to her and Chuck's PA and she had a bounty of invites to sift through whilst Henry napped. Eventually she decided on a party for alumni of something called the New York Academy of Dramatic Arts. Free food, drinks and the alumni would even entertain the party with their singing. It sounded perfectly pleasant and not too wild or corporate for Blair. She wouldn't have to sweet talk her way into anything, in fact, people would be lining up to schmooze her out of a couple hundred grand for their university. So, after finding an appropriate outfit, and fixing herself up, she called a town car for herself, and left Henry sleeping with Dorota on guard, kissing her son's forehead before leaving The Empire.

A twenty minute car ride later, and she had arrived at the NYADA party in a fancy dining room in a hotel that, not surprisingly, was partly owned by Chuck. She was instantly greeted by a smartly dressed waiter with a plate of champagne glasses, which she gratefully took one from. The waiter with his slick backed hair welcomed her to the hotel and offered to escort her to the room. After correcting him greeting her as 'Ms. Waldorf' ('Mrs. Waldorf-Bass. No more, no less.') and taking a long sip of the dom in her glass, she was led to the room filled with smartly dressed people, and none of them were going to spit up on her.

A elderly woman jumped on Blair the second the french doors revealed her, an annoyance Blair hadn't experienced in so long that it was almost welcoming. She quickly learnt that the woman, Irene, was the dean of admissions at NYADA and the hostess. She was also a friend of Blair's mother's. So, whilst alumni sang on a makeshift stage which had a small five piece band and a microphone, a red velvet curtain as a backdrop, Blair and Irene exchanged pleasant conversation, stopping only to exchange greetings with people who approached the two of them.

"So, how's your husband? And your son? I must say that your mother showed me some pictures of the three of you, you all look so well." The woman asked her about twenty minutes into their conversations, Blair sipping her drink politely with a smile when her husband and son were mentioned. She couldn't help it. The very thought of Chuck and Henry made her smile like an idiot. She quickly assured Irene that her child and Chuck were both fine, Henry was growing beautifully and Chuck was doing just as well, and his business was flourishing. "Are you two thinking of having any more kids soon?" The question made Blair almost choke on the champagne she was sipping, but a quick recovery saved her from the embarrassment.

"Nothing's in the cards at the moment. Henry's only eleven months old and Chuck and I are still in the spoiling him rotten with love and affection." _And toys and teddies. _She added mentally as she smiled and cleared her throat. The woman looked unsatisfied with this answer, tilting her head slightly, to which Blair gave a tight smile and straightened up slightly. "You see-" Before Blair could form a rebuttal, something in the background distracted her. She turned towards the stage, where a petite, brunette like herself was standing in front of the microphone, softly crooning a song that Blair knew too well.

_Moon river, wider than a mile_  
_I'm crossing you in style some day_  
_Oh, dream maker, you heart breaker_  
_Wherever you're goin', i'm goin' your way_

Blair tilted her head slightly as she listened to the brunette softly sing her own rendition of the song Blair had listened to thousands of times whilst watching Breakfast At Tiffany's. She even played it in the background whilst she would be trying to put Henry down to sleep. Normally Blair would have bitten off the head of the person who thought they could do Audrey justice, but this woman on the stage seemed to do a pretty good job. With a quick turn of her head to Irene and a few words, she learnt that the singer on the stage was Rachel Berry, soon to be the next Elphaba in Wicked and she had attended the university a year ago, after graduating a year early and getting a full scholarship. By the time the overview of Rachel Berry had been given, the song was finished and the brunette stepped off the stage.

"Excuse me." Blair was making history here, approaching someone herself without wanting something from them. The brunette looked up from the glass of champagne she was staring down into with intent to see Blair walking towards her. Obviously, Rachel recognized her from the look on her face, everyone on the Upper East Side knew who the Basses were. Chuck owned or was invested or had connections with nearly every part of the Upper East Side, which made Blair the Queen of the joint. "I'm Blair Waldorf-Bass. I just wanted to say that your song was brilliant. I've always had a bit of a soft spot for Breakfast At Tiffany's." She explained, offering her hand to Rachel, who looked like a rabbit in the headlight. Either way the girl shook her hand.

"Thanks, me too. It's one of my favorite non-musical movies." Rachel replied, having recovered from the shock of being in the presence of the Princess of Manhattan. "I guess I should tell you to pass some thanks onto your husband for his generous donation to the Gershwin theatre last year. He pretty much saved the place from being sold and converted into a chain store." She added before taking a sip of her drink as Blair did the same. Blair remembered the saving the theatre well, Chuck had had a party thrown in his honor and Blair was heavily pregnant with Henry at the time, so naturally she'd had no fun there.

"I'll be sure to pass on the message." Blair assured the woman "So, Irene tells me you're set to be in Wicked. Tell me more about it." And that's how it started, the two girls chatted for what felt like hours about Rachel's rehearsals, her time in NYADA, Blair's reasons for escaping The Empire for the night. They even exchanged a brief discussion about her wedding, which Blair was strangely secretive about. Blair found herself enjoying her time in Rachel's presence, which led to her asking something of the woman she never thought she'd ask. "I'd like to have lunch with you sometime. How does tomorrow sound?" Blair asked as the night drew to a close and she could practically hear the town car's driver waiting breath out in street to take her back home.

Rachel looked shocked but nodded and smiled. "That sounds lovely, Mrs. Waldorf-Bass."

"Call me Blair." Blair replied without missing a beat as she smiled.

* * *

Chuck was sat on the couch of the penthouse as he went through some paperwork, Henry playing with some bricks on the play mat that took up most of the room as his father kept one eye on the boy. Dorota was in the kitchen baking cookies like she normally did so Blair and Henry had a constant stream of her delicious baked goods available to them and Blair herself was walking out of the elevator with a soft smile on her face. Chuck stood up from what he was doing and helped his wife out her coat, kissing her lips softly as he intercepted her. Blair smiled contently and greeted her husband in a similar fashion before walking over to her son and scooping him off the floor and kissing the top of his head.

"Lunch with Rachel again?" Chuck asked curiously as Blair sat on her knees on the floor and helped Henry build his blocks. "I must say you two have struck up quite the friendship, yet you hide her away from me. Even Henry met her last week. I tried to bribe him with one of Dorota's cookies to give me the details of their meeting but he's a tough nut to crack. And he can't speak yet. Either way I get the feeling that I should be offended?" Chuck asked teasingly as he walked over, admiring his wife and child looking perfectly domestic and beautiful. Before Blair could quip back, Chuck's phone rang and he held up a gentle, polite finger to Blair, picking up the phone and holding it to his ear. "Chuck Bass...Jesse St James, nice to talk again...Yes, the dinner with your sister and brother is still on...No, I haven't changed my mind and bankrupted your brother yet...All right, I'll see you, Ariella and Michael tonight then." And with that, the conversation was over.

"Jesse St James? Isn't that the guy who won the Tony award last year?" Blair asked as Henry began to offer his sock to his mother. She smiled and took the ducky patterned sock from her baby, only to replace it back onto his tiny feet. Chuck nodded and sat on the couch.

"Old family friends. His brother's law firm has been trying to catch me out for years now. The owner is good friends with my dear Uncle. Michael St James is however a powerful person to have on my side, the problem being Jesse hates the guy." He explained as Dorota entered from the kitchen with a plate of cookies. Henry clocked onto the potent smell and began crawling towards the maid, Blair having to catch the toddler up, plucking him off course in his crawling and bring him back to her lap. "Either way, I'm going to dinner with Jesse, Michael and their youngest sister, Ariella, who's training to be a doctor. You're more than welcome to join me." He explained as Dorota offered a cookie to Henry, ruffling his hair and he politely took one from the plate, Blair following suit.

"I'll have to pass, I have to meet with the decorators about updating Henry's room and my mother is popping over for her weekly dose of our son." She explained with a smile, nodding to Henry who was now dissecting the cookie in his hands. "So, don't be too late." She added with her trademark look that was their code for 'good thing we have sound proof bedroom walls'. Chuck assured his wife that he would be home before the clock struck 10 and smirked at his good fortune.

* * *

The dinner with the St James' went exactly as Chuck has suspected. The two brothers could barely stand to be in the same room as each other, and their younger sister just tried to get through the evening without a fight or drama. Chuck and Ariella buffered the two boys at their table in the fine dining restaurant they'd picked and kept the drinks flowing throughout the evening. Jesse and Chuck were about the same age so easily to talk to than the pushing 30 Michael or the barely 20 Ariella. They discussed Ariella's work in the War Memorial Hospital she was training in, and Jesse's work as Sweeney Todd (Michael scoffed an unimaginable amount of times through this period of time where Jesse spoke about his work) and Michael spoke briefly about his work at the law firm. Chuck made a few good natured quips about Michael's boss that would have made Blair proud and shut the elder brother up.

"So, how's the missus? I see she hasn't joined us this evening." Michael asked between sips of his wine curiously as the evening drew to a close and Ariella looked up from pushing her strawberry cheese cake around her plate delicately. Chuck smirked.

"Your observation skills are top notch, Michael, I bet they appreciate that at the firm." He quipped as he refilled his glass with the expensive wine he'd brought. "Blair is spending time with our son and her mother. She sends her well wishes and regrets she could not attend tonight. Maybe some other time." He replied simply, the final part being just a nicety that had no substance. He had no intentions of letting Michael St James anywhere near his son or wife. He'd sooner invite his uncle Jack to Thanksgiving dinner. Jesse seemed to recognize the hollow promise in his words and smirked into his own glass, Ariella herself smiled and popped some cheese cake into her mouth. "What about you, Michael? If we're discussing bringing partners tonight, you could have brought your girlfriend. Or your wife if she's unavailable." He smirked as he spoke.

Michael St James fumed silently and stood up, taking a hundred dollar bill out his pocket and placed it on the table before starting towards the door, taking his coat and shrugging it on as he walked out. A couple seconds later and the entire table brought into laughter, Ariella giggled guilty into her dessert as Jesse laughed wholly. Chuck smirked and took another bite of his dessert. "That might have made my week. Michael having a temper tantrum." Jesse told him with a smile as he sipped his drink. "Definitely cheered me up, kudos to you, Chuck." He smirked as Ariella smacked her brother half heartedly and told him to behave. Chuck just smiled and refilled the middle St James' wine glass.

"My pleasure. Someone needs to put the dick in his place, if you'll pardon my language." He explained, casting Ariella a look as he spoke. "Speaking of partners, I hear you're sowing your oats. Recent conquests including Natasha Hamilton. Her father wouldn't stop banging on about his princess' broken heart the other week, telling me 'God forbid the son of a bitch that spits on any daughters you have'." Chuck told him as he sipped from his glass. The man was right, Chuck Bass would make any man who dared hurt any daughter of his disappear completely. He was a very protective man over the people he loved. Jesse ducked his head and smirked.

"Natasha is a very good actress, both on the stage and when she's acting like would-be Princess of New York. She was stringing me along for my connections in the acting world, connections Daddy Dearest can't get. So when the jig was up, she acted like I drowned that rat of a dog of hers and now her father hates my guts." Jesse explained with a smirk. Chuck smirked at the idea that there was a woman out there who thought she could take Blair's place as New York royalty. Ariella looked pratically mortified by this conversation, her cheeks red. "Still, not the worse way I've ended a relationship. I've done far worse than not let a girl take advantage of my friends." He mournfully told his wine.

"Oh, god. Not her again." Ariella muttered.

"Who's her?" Chuck asked, ticking an eyebrow curiously.

"Rachel Berry."

* * *

"...So she went off with this Finn, who sounds like a dick from what I hear." Chuck finished recounting Jesse's drunken rambling about the girl who had broken his heart to Blair as she paced back and forth with Henry sleeping in her arms. Chuck sat in the armchair they had in Henry's room and spoke as Blair hummed lowly to Henry and listened to the gossip he'd picked up at dinner.

"Language."

"My apologizes." Chuck replied with a smirk. "Anyways, Jesse seemed rather heartbroken over this girl, even though he last saw her years ago. I felt I could relate to his vendetta against this insolent idiot who'd stolen his girl and hoped him the best in the future. I always warned him not to give up on this girl, I mean, I didn't give up on mine." As he continued, Blair began to lay their son in his crib, humming into his forehead as she did. Blair shot her husband a soft smile over his shoulder and leaned on the railing of the cot as he spoke. She then leaned back down and kissed Henry's head as he sucked his thumb, tucking him into the blanket he'd slept with every night since he was born.

"Good night, my prince." Blair told her son before turning off the light and setting the mobile turning, playing out a soft lullaby. Chuck smiled, stood and kissed Henry's forehead himself before wrapping his arm around Blair's waist and escorting her out the nursery. The two closed the door behind their son and started down the hall towards their own bed. Blair walked into the walk in wardrobe and began to strip off her dress and hang it up. "This Jesse St James needs a girl. A substantial woman who's not just easy on the eyes but good for him. And I know just the girl." Blair emerged from the wardrobe in a silk nightie as Chuck undid his tie, a sparkle in her eyes that Chuck only described as the 'Queen B sparkle'.

"I know that look." Chuck told her. She smiled and leaned against the door frame. "Fine, but I want to meet the girl first."

"Deal. I think you'll like my selection in match making." Blair replied as she brushed out her hair and undid her necklace, placing it in her trinket box on her vanity. She smirked and moved onto to where Chuck was undoing his cuffs and watching his wife walk towards him. She slowly placed kisses on her husband's neck. "I told you not to be late. And you made good on your promise." She murmured seductively. Chuck quickly whirled around to place a hot kiss on his wife's lips before leading her to their bad. Good thing they have sound proof bedroom walls.

* * *

The next day, the Bass family prepared to welcome Rachel Berry into their suite. Chuck was replying to some work emails as Blair and Dorota played with Henry on the play mat. The elevator dinged and Rachel walked into the living room. Blair instantly jumped up and kissed the woman's cheek as she greeted her friend. Henry also recognized Rachel and began squirming in his grumpy way to see the woman. "Someone is a bit grumpy." Dorota commented on the boy as he whined; Chuck stood up to approach the two women who were chatting as Rachel peeled off her coat and hung it up herself as if she knew the apartment by heart already.

"Chuck, allow me to introduce Rachel Berry." Blair smiled triumphantly as the girl extended her hand to Chuck. He had to stop his jaw from hitting the floor as he took the woman's hand and shook it. Rachel Berry. Blair wanted to match Jesse St James with the girl he'd been pining over for years. Either this was the world's weirdest coincidence or Blair knew all along. He managed to recover from the shock rather quickly and smiled at the girl as Dorota brought over a still whining Henry, who was reaching for his mother or Rachel or who will pay him attention. Blair plucked Henry from Dorota's arms and started to hum.

"Chuck Bass. And before we start, I want to thank you for getting Blair's sanity back. She's been needing a friend such as yourself for a while and there you were." He complimented the woman, who blushed deeply and thanked him for the comment. Chuck had to tell Jesse about this. This was just brilliant. He needed a reason to leave the room, so as always, he used the youngest Bass. "Now, I'll leave you two ladies to get drinks whilst I put Master. Bass down for his afternoon nap." He smirked and gently took Henry from Blair's arms, kissing Blair's forehead and then Henry's before slowly walking him towards the nursery, Dorota following suit. Once he was in the nursery and pacing slowly back and forth with a whining Henry, Dorota putting on the mobile and setting up the baby monitors for them, Chuck pulled his phone out of one pocket and dialled Jesse's number.

"Jesse, its Chuck. Listen, my wife is attempting to set you up. And you'll never guess who with..."

* * *

"I'm s-sorry? What did you just say?" Ariella St James looked up as Jesse asked the person on the other line to repeat what he'd just said as they sat on the circle seats of the theatre her brother performed in. He picked a different seat every day so no one could find him during his lunch breaks. Sadly, his little sister had found him and was sitting next to him tucking into a subway sandwich. She needed it after a 36 hour shift at the hospital. She'd rather sleep but she promised her mother that she would talk to her brothers more often. So here she was, her in her doctor's coat and Jesse in his rehearsal gear as they both tucked into a deli sub. "Your wife is trying to match me with the girl I told you about the other night, completely coincidentally?" Jesse asked incredulously.

Ariella's head shot up when she heard this and licked her lips of melted cheese as her brother spoke on the phone. She assumed he was talking to Chuck Bass from what she gathered, context wise. Jesse had left his meal untouched as he continued to take in more information. "Uh huh...right..." Ariella watched as Jesse pinched the bridge of his nose and sighed heavily. "I guess that it can't hurt too much...Right, I'll await Blair's call...Talk to you later..." Jesse pressed end call on his phone and threw it onto the seat next to him. He shoved the chicken and bacon ranch between his lips and took a bite. He stared ahead at the stage with a vacant expression that Ariella knew all too well.

"Um, you okay...?" She asked curiously before taking another bite of her sandwich.

"Chuck's wife, Blair has decided to match make me...with Rachel." He explained with a huff, taking a sip of his water. Ariella popped her eyebrows in surprise at this news and bit her lip. Ariella had been there when Jesse had first fallen for Rachel. She, to this day, hadn't seen him so happy than when he was talking about Rachel or was with her. And she'd seen the heartbreaking stage of mourning when they broke up. So, she was a bit wary about her brother's emotional state at the idea of seeing her again after all these years. "Someone up there has it in for me. I bet it's Nana." He murmured before taking another bite of his sandwich with a sigh.

"You don't have to see her, Jess." Ariella offered gently as she sipped her soda. "And Nana loved you. She only hated me because I didn't want to be a debutante, socialite wife of someone who plays golf with drug lords and politicians." She added.

"But what if this is fate? What if I was supposed to tell Chuck so Blair could get match us together? What if it's fate that we had dinner with the husband of someone who could give me a chance to see her again? I mean, what if it was fate that Michael, the dick he is, brought up partners at the dinner?" He asked her softly, looking his sister deep in the eyes with a look he recognized from the day he'd come home shaking and crying about eggs and Rachel. Ariella sighed and leaned over to ruffle her brother's curls comfortingly. He instantly went to fix his curls and she chuckled.

"Then, go for it."

* * *

"..So you never did tell me how the date went yesterday." Blair stated as Dorota handed the girls their cups of tea. Blair and Rachel were sat on the couch as Henry tried to pull himself up on the leather, his brow knitted in concentration as he did. Blair smiled and ruffled her son's hair when he fell back once more. Rachel stirred her tea shiftily and blushed into her tea as she added sugar. Dorota and Blair exchanged a look over her behavior as the maid, who was more a friend and confidante than the help, sat down on the couch besides Blair as Henry continued to try and stand by himself. "What's that look? You should be all doe-y eyed and thanking me for hooking you two up. You should be kissing my feet for my genius match making skills right now. So, why are you sulking into your cup?"

"I know you meant well getting Jesse and I on a date together. But...I already knew him." Blair almost dropped her cup at this admission. Dorota made a face and stared intently at her tea. "Me and Jesse dated in High School, it was epic, once in a lifetime love, but it's gone now. Our combined efforts broke it. I went off with the wrong guy and he cracked an egg on my head. We did a bit of off and on the next couple years but once I graduated, we never saw each other again." She explained with a shrug. Mrs. Bass put down her cup and put both hands on her chest dramatically.

"Rachel, I'm so sorry if your feelings were hurt, and I'm fully prepared to have him fired or get someone to steal his tony award if he was even the slightest bit mean to you!" Blair told her friend, tucking some hair behind her ear as she spoke fast and guiltily. But then she went over what Rachel had said in her mind. "Wait...High School? Some guy?...Oh sweet Mary, Jesus and Joesph, you were the girl he was talking about to Chuck?"

"I'm sorry, what?"

"What happened last night?" Blair inquired, "Come on, I need to know!"

"Um, we chatted, dined, avoided conversation about High School, drank a wine. It was l-lovely." Rachel told the two women. Dorota nodded and gestured for her to continue, sensing there was more. "But then, we were sharing a cab and...we kissed. All these feelings came flooding back and I had to get out of there as soon as possible. We had a small argument about my not wanting to talk about what had happened and I walked the whole way home." She explained, taking a small sip of her tea as she did. Henry interrupted the silence by making a sound of immense concentration as he pulled himself up on the couch shakily. "I don't think me and him could ever work out, Blair."

The smirk on Blair's face said one thing only. Wanna bet?

* * *

"...So we argued, shouted a bit then she stormed out the cab." Jesse finished as he shot a yellow ball into the pocket. Chuck was leaning on a wall with his own pool stick and a glass of bourbon. He'd decided to check up on Jesse after his date with the love of his life yesterday. "It didn't go well, and the whole ordeal was Blair's fault. And yours for blabbering about it to her." He added.

"Yes, but up until that point at the end of the evening, you seemed to be having a charming evening full of laughs and smiles and flirting." Chuck sniped back before stepping forward to pot one of his own balls into the pockets. He sipped his bourbon and gave Jesse a look. "The way I see it, you two just had a rough start and need to just talk out everything that's happened between you. It's pretty simple when you think about it actually." Chuck said as he walked around the table to Jesse's side and spoke slowly with a small shrug as he did.

"It's not that simple." was Jesse's only reply.

* * *

"We need to get those two together. They're just being stubborn about wanting to talk their problems out, and they need a push from us." Blair announced once Chuck finished telling her about his conversation with Jesse. The two were sat having lunch in the dining room, Blair nibbling at the fruit salad she had in front of her. Chuck took a sip of his coffee and popped his eyebrows. She smiled in a scheming fashion and popped a strawberry into her mouth. Chuck sipped again at his coffee again and hummed curiously as Blair pushed her fruit around her plate. The couple were enjoying a day alone as Eleanor had woken the pair up, standing at the end of their bed with Henry in her arms before announcing she had decided to take Henry out for the day. Blair was so sleep deprived as of late that she'd given a lazy thumbs up and turned over in bed and let Chuck work out the details of the grandmother-son play date.

"I'm starting to struggle to remember a time where 40% of our conversations didn't revolve around Rachel Berry and Jesse St James." He quipped gently, taking his wife's hand off the table where it lay absently and brought it to his lips. Blair smiled and chuckled. "How exactly are we going to get them to talk it out? They're two independent people, and I don't think we can bribe them into talking." He added a few seconds later.

"Maybe not, but we could always force them..." Blair mused, taking a sip of her ice tea as she thought. Chuck could practically see the light bulb flash on above her head as her eyes sparkled and he knew she had the answer. "It has been a while since we've had a function after all..."

* * *

"Blair, why have you dragged me here? And why did you insist that I wear Alexander McQueen?" Rachel asked as she walked into the Waldorf family home, where people she didn't know were milling around and exchanging small talk. Blair was dressed in a fabulous dress as per usual and pulling the girl along.

"Because Chuck and I decided to throw a party to raise money for arts programs in New York schools, and who better to attend than a future Tony winner such as yourself! And The Alexander McQueen was a well needed suggestion. Besides you look adorable in that dress." Blair added as she took two champagne glasses and handed one to Rachel. The brunette's eyebrow popped and she took a sip of the bubbly, looking down at the flowery pattern sun dress made of silk she was wearing, her hair in curls around her face. "We like being charitable and we know how much the arts mean to you. There's also some people here that could really benefit your future. You're welcome." Blair explained, gesturing with her hands when she said you're welcome. Rachel chuckled and took another sip, rolling her eyes and submitting to the party atmosphere.

"Fine. But I have to meet my parents at 4pm." Rachel explained.

"I will make sure a car is ready to deliver you onto your fathers by 3:30." Blair assured, taking another sip of the champagne. "Now, I have someone I want you to meet." She took the girl's wrist and started to lead her to the Waldorf's dining room. Rachel let Blair drag her along, having to jog in her 5inch heels to keep up with Blair's determined gait. They quickly approached the double doors that led to the dining room, Blair snapped the door open, gesturing for Rachel to walk inside, which she did a few moments later. Blair hovered in the doorway to the room as Rachel stepped into the room and looked around, quickly noticing something odd and curly haired standing in the corner of the room.

"J-Jesse?"

"Rachel."

"What's that, Dorota? Henry wants me? Okay, coming!" Blair called out, pulling the door shut and twisting the key in the lock before Jesse or Rachel could react. "You can come out when you've talked." Blair told the couple through the oak door before popping the key into her purse proudly. She smirked and turned to see her husband standing behind her holding another identical key to the other entrance to the dining room. "Nicely done, Mr. Bass." She smiled, taking the key from him and letting it join its twin in her Prada clutch. She then turned to press her ear against the door to try and listen in on their conversation. Chuck smirked and wrapped his arm around her waist to try and lead her away. "Come on, aren't you the slightest bit curious?"

"Some things are better private, sweetheart." Chuck reminded her, kissing her forehead and tugging her away from the door. Blair quickly ordered one of the waiters to guard the doors, making the poor lad shake and nod scared for his job. "Come on, Blair, your public miss you."

* * *

Blair unlocked one of the doors at 3pm, two hours after her initial imprisoning the two of them then bolted in case they jumped up at her. Chuck and Blair decided to let them emerge themselves when they were ready, seeing as the shouting had stopped about an hour ago, most of it muffled by the excellence of the walls. Blair sipped nervously at glasses of champagne and later, iced teas as the party guests began to file out of the Waldorf's home one by one until just Dorota, Chuck, Blair and Henry were left, sitting around waiting for Jesse and Rachel to emerge.

"Perhaps they killed each other...?" Blair guessed lightly. "I knew we should have cleared away the cutlery." She murmured as Henry sat in her lap, playing with his mother's diamond bracelet, a gift from Chuck.

"I'm sure they haven't killed each other, Blair. You really need to stop worrying about The Hunger Games becoming real life." Chuck muttered.

"It could happen!"

Chuck was about to retort, but was interrupted by the sound of a doorknob turning and the four people turned to see the duo emerge slowly from the room. Obviously not having noticed the people staring at them as they walked out, their hands were entwined and they were staring intently at each other adoringly. To add to that evidence, Rachel's hair was disheveled and Jesse was failing to hide a hickey with his polo shirt. Blair raised her eyebrows and stroked her son's hair as the onlookers watched St James and Berry close the door behind themselves and finally notice them sitting there. "Hello, sluts." was Blair's opening statement, covering her son's ears as she spoke, making sure he didn't hear the profanity though she was only teasing. "I hope I don't have to disinfect that dining table, I eat off that thing." She added, cuing a blush from Rachel's face and a nervous chuckle from Jesse.

* * *

"Make a wish, Henry!" Blair cooed as Dorota placed the birthday cake in front of Henry in his high chair. The toddler shook his fists happily at the sight of the cake and he made a half-hearted attempt to blow out the small candle shaped like the number 'one' on top of the small cake. Blair chuckled and leaned over to blow the candle out, causing her son to clap happily and smile up at his mummy. The people around the table clapped happily as this happened, Rachel handling the camera to document the occasion. Blair returned to her seat as Dorota began to slice off pieces of the cake for the four adults around the table, planning to give jelly to Henry. Rachel and Jesse took their pieces as they sat next to each other, Blair and Chuck on the other side.

"No cake for me, Dorota. The thought of eating cake right now...just ugh." Blair told the maid, crinkling her nose delicately. "I'll stick with my chocolate strawberries, thank you very much." She smiled, gesturing to bowl in front of her. Rachel smiled as she took a bite of her cake, Jesse leaning over to kiss her forehead softly. "So, how is things going for you two? Isn't it your one month anniversary on Saturday?" She asked the two lovebirds as Dorota handed Chuck some cake.

"Fine...just fine." Rachel blushed brightly and tucked some of her hair behind her ear as she took another bite of cake.

"We're going to try things slow." Jesse supplied as he took a sip of his coffee.

"That's not how it looked when you came out my dining room." Blair quipped lightly as she popped a strawberry between her lips. Before Jesse and Rachel could insist that nothing happened and the extreme disinfection Blair had put her table through was in vain, she spat the strawberry back into her hand. "Ew, this tastes rotten. These strawberries must be off." She complained, inspecting the chewed piece of strawberry. Chuck looked over at his wife and picked another strawberry dipped in dark chocolate from the bowl, taking a bite. Rachel did the same, both chewing a considerably piece off their chosen fruit.

"Blair, it tastes fine." Rachel told her. Chuck confirmed this a few seconds later.

"Oh my god, I probably have an incurable disease that affects my ability to enjoy fruit!" Blair panicked, wiping the chewed up piece of strawberry into her napkin as Dorota put the jelly in front of her son. Blair sighed and put her head in her hands. Chuck laughed at his wife's dramatics and leaned over to kiss his wife's hair reassuringly as Dorota rushed to Blair's side to console her. Jesse and Rachel exchanged a look.

"Don't worry, Miss Blair. You may not have terminal disease. Perhaps you're just pregnant." This didn't console Blair. Her head popped up and she asked Dorota to repeat the last part again very slowly. When she did, with an added explanation that sometimes pregnancy turns women off certain foods, there was a brief couple of moments' silence between the people in the room, broken by Henry's squealing at how the jelly wobbled.

"How's that for ironic, huh, Blair?" Chuck decided to break the silence. "You decided to get these two together to try and get some time away from your offspring and you end up with another on the way." He chuckled, taking a smug bite of his cake, waving his fork at Jesse and Rachel when he spoke of them. Blair gave Chuck a small glare which he rebutted with a kiss against her nose. Rachel smiled supportively and chuckled at the two's dynamic. Jesse took her hand from where it sat on the table and squeezed it gently as the two watched the Basses deal with the news that they had another child on the way.

"This is your fault, Charles Bass." She grumbled.

"I know, sweetheart."


End file.
